Ammonia → (R)-1-[2-(2, 3-methylenedioxyphenyl) heptyl]-3-[4, 6-bis (dimethylamino) pyrimidine-5-yl]urea

Participants

Reaction Steps

To a solution of 23.78 g (0.1405 mol) of 5-amino-4, 6-bis (dimethylamino) pyrimidine in 476 ml of methylene chloride were added 17.4 g (0.0586 mol) of bis(trichloromethyl) carbonate (namely triphosgene) and 34.1 g (0.337 mol) of triethylamine, and the resultant mixture was refluxed with heating for 1.5 hours. The reaction mixture was allowed to cool at room temperature, mixed with 33.0 g (0.1402 mol) of (R)-2-(2, 3-methylenedioxyphenyl)-heptylamine and allowed to react at room temperature overnight. The reaction mixture was mixed with a small amount of aqueous ammonia and water, and the aqueous layer was extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was chromatographed on a silica gel column, eluting with chloroform-1% methanol/chloroform-2% methanol/chloroform and recrystallized from heptane and ethyl acetate to give 41.0 g of the titled compound.

Provenance & Evidence